


The Best Worst Wingman

by TheSeeingStar



Category: Critical Role (Web Series)
Genre: F/F, F/M, Friendship, Humour, Potential tiny episode 85 spoiler, Uncomfortable Flirting
Language: English
Status: Completed
Published: 2019-12-13
Updated: 2019-12-13
Packaged: 2021-02-26 06:07:59
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,404
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21778813
Author URL: https://archiveofourown.org/users/TheSeeingStar/pseuds/TheSeeingStar
Summary: After he loses a bet with Beau earlier in the day, Caleb finds himself in an uncomfortable situation...(Rated T for language and suggestion)
Comments: 1
Kudos: 39





	The Best Worst Wingman

"I’m not doing it."

"Now Caleb," Beau tutted, a shit eating grin plastered on her face, "you promised. Come on, it won’t be that bad. Just be yourself, that’s all I ask."

"Charming. I thought I wasn’t allowed to mention your sex life, now I’m helping you achieve it?" The wizard scowled, hunching down in his chair in the vague hope that he might disappear into the floor if he tried hard enough.

"The ends justify the means my friend. Now off you go." She gestured towards the bar. Beside her, Jester and Fjord snickered, obviously loving every minute. At least Cad and Yasha weren’t here to witness this, both having retired to bed already. 

"Don’t listen to her CayCay, you can do this." Nott slurred drunkenly from her position slumped on the table to his left, barely awake. "You’re intelligent, you’re capable, you're clever, you’re smart, you’re sexy..." Wait what...? He thought to himself. Glancing at Beau in surprise she looked sheepish but kept quiet. He filed that thought away to ask about in the morning, if he didn’t die from embarrassment before then. Nott continued on oblivious, lifting her head from the table just enough to smirk at him, twirling a shaky finger towards him what he supposed was meant to be suggestively. "You could have any girl you wanted! Play your cards right, woo her a little bit, use the old Widogast charm, and you could end up finally getting some ass tonight. You got this!" She collapsed back on the table, letting out a little snore.

"What the fuck was that?" Fjord asked between chuckles. Jester was almost crying with laughter now too. He realised belatedly that his cheeks had turned beet red.

"Don’t you dare steal my prospective lay Widogast." Beau scowled. A part of him felt like taking up the challenge, bringing out a little of the Bren of the old days and charming the woman standing alone at the bar, fortunately oblivious to their conversation. He shook that thought away quickly, he was not that man any more. Self-restraint was his friend now.

"I can think of nothing I want less Beauregard." He responded dryly.

"Good. Now go."

Reluctantly, he downed the last quarter of his tankard of ale and stood. Taking a few steadying breaths to calm his nerves and attempting to shrug at least some of the tension from his shoulders, he turned and started for the bar, thankful that he was at least a little tipsy. On the way there, he made sure to mentally berate himself for the thousandth time for taking that stupid bet with Beau earlier on in the day. Of course she’d been able to beat Nott again in a race up a tree. He should have seen it coming. If he’d won though, Beau had agreed to buy him any book he wanted from the quaint dusty bookshop in the small town they were staying in, and it had definitely been worth the risk at the time.

Predictably, Nott had lost. And so here he was sweating profusely as he made his way over to what surely must be one of the most beautiful women he had ever seen. Beautiful flowing wavy locks the colour of fire... well not the colour exactly, multiple colours. It seemed to shift and flicker, not quite as though it were really made of flame, but more like an image of flames being projected onto it. It was mesmerising. From that and her faintly glowing copper skin, he could identify that she was a fire genasi, though he’d never met one in person before. A wide brimmed leather hat sat beside her on the bar and she wore plain, well used travel clothes, but there was something about the way she carried herself that made Caleb sure she would look good even in a burlap sack.

She was clearly a very confident individual, and while that was attractive, it set Caleb on edge to know he would come across so obviously awkward in comparison. Then again, that was the whole point of this. He hated that, it felt so manipulative. The plan was for him to talk to her, weird her out to the point that she needed rescuing, ready for Beau to come and "save" her from him and... well the rest Caleb didn’t want to think about.

He salved his conscience with the knowledge that he wouldn’t even have to try to make her feel uncomfortable, so it wasn’t technically manipulation. Just Beau using him as a tool to get her leg over. He shivered uncomfortably at the thought, arriving at the bar beside the woman. The bartender, a heavyset Orc, plodded over.

"Drink?" He ground out, wonky fangs protruding from his bottom lip to almost meet in the middle of his face and pinch his bulbous nose.

"Ale, please. And whatever the lady would like too." He tried to sound convincing, really he did, but this wasn’t his style. Not any more anyway. Sixteen year old Bren had had plenty of game...

She looked up from her own tankard and smiled, the tired amusement of someone well used to this scenario. "Thank you. And what’s your name?"

"Caleb." He smiled back, knowing it didn’t reach his eyes. "And yours?"

"Idina."

A silence stretched between them, and even when the Orc delivered their drinks with a graceless thud, a few drops of ale slopping onto the bar with the force, he couldn’t think of what to say to her next. Idina downed the last of her original pint, and he looked to Beau desperately. The monk only grinned and waved her hand for him to continue.

"Forgive me Caleb," he jumped, eyes finding hers again, "but you don’t seem the usual type to try it on. It happens a lot you see, it’s probably the hair or something I don't know." She shrugged, picking up her new drink. "They buy a drink, invade my space, drop an embarrassing pick up line. Sometimes I don’t even get the drink, outrageous..." She grinned, leaning in closer, "so tell me. Are you in the habit of buying women drinks in bars to be nice, or are you just shy?"

"I’m... shy...?" he stuttered out.

"Mmhm. And really?"

"...Really?"

"Which of your friends sent you over to set up the knight in shining armour routine?"

His eyes went wide, mouth working open and closed soundlessly for a moment.

"She’s uhh... Dark skin, dark hair, abs." He managed eventually. Idina looked over, giving Beau an appraising look.

"Fit. I would have said yes even without the terrible attempt to play me." She picked up her drink, edging away from him, body language becoming uncomfortable, though facing back towards the bar, the smirk on her lips told a different story. "Can’t play a player. Let’s at least pretend you did a good job and I didn’t notice."

"You’re not... cross?"

"No Sweet, what’s to be cross about? At the end of the day, a lay's a lay and like I said, she’s fit." She gave a small shiver, rubbing her arms and glancing around, putting on a show of needing help. Caleb smiled relievedly into his drink.

"Thank you."

"You’re welcome." Out of the corner of his eye he saw Beau stand, finally ready to make her big entrance. "You’re pretty hot as well you know, fancy joining us?"

He nearly spat out his drink, coughing into his hand as Beau rocked up. Idina winked suggestively, her grin fading to a practiced grimace in perfect time for the monk to walk up behind her. 

"I am so sorry about him, Caleb, what have we told you before about trying it on with women in bars. It’s degrading man, come on." Beau tutted at him for show. "I’m Beau by the way." She edged in between the two of them, turning her back on Caleb, her attention diverted.

"My sincere apologies, it won’t happen again." He looked pointedly at Beau, who simply waved him away. Idina shot him a small smirk before he turned away, and he returned the gesture with a shy smile before escaping back to their table, taking his drink with him.

"So, how did it go? Looks like it worked?" Jester whispered loudly, looking between him and the two women flirting with each other at the bar.

"Like clockwork." Caleb smiled, taking a long drink.


End file.
